Phoenix/ Health & Lifestyle
Published on July 10, 2019
Festival travel: Escape from Phoenix to Chicago for LollapaloozaPhoto: iStock

It's the grandaddy of modern music festivals and it's still going strong. Book your trip to Chicago from Aug. 1-4 for this year's Lollapalooza.

Headline acts include The Strokes, Childish Gambino and Ariana Grande, but over 170 acts from all over the world will play the festival's eight stages. Offstage look for plenty of food and drinks, merch and kid-friendly offerings, along with space for visual arts.

The festival plays out in Grant Park, nestled in the Windy City's Loop overlooking Lake Michigan and convenient to the city's vast cultural and culinary offerings.

Whether you’re ready to book your trip now or just wondering what it would cost, take a look at these forthcoming flights between Phoenix and Chicago, which we pulled from travel site Skyscanner.

We've also included popular hotels, restaurants, and attractions in Chicago, to round out any visit. (Prices and availability are current as of publication and subject to change.)

Hoodline offers data-driven analysis of local happenings and trends across cities. Links included in the articles may earn Hoodline a commission on clicks and transactions.

Flight deals to Chicago

The cheapest flights between Phoenix and Chicago are if you leave on Aug. 1 and return from Illinois on Aug. 7. Delta currently has roundtrip, nonstop tickets for $247.

If you fly out of Phoenix on Aug. 1 and return from Chicago on Aug. 6, Sun Country Airlines can get you there and back for $312 roundtrip.

Top Chicago accommodations

To plan your accommodations, here are two of Chicago’s top-rated hotels, according to Skyscanner, that we selected based on price, proximity to things to do and customer satisfaction.

The Palmer House a Hilton House (17 E. Monroe St.)

Photo: Trip by Skyscanner

If you're looking for an inexpensive place to stay, consider The Palmer House a Hilton House. The hotel has a 4.5-star rating on Skyscanner, and rooms are currently available for $92.

The hotel is within walking distance of the best attractions the city of Chicago has to offer, like Millennium Park, Grant Park, Lake Michigan, the Art Institute of Chicago, the theater district and the Magnificent Mile.

The Raffaello Hotel (201 E. Delaware Place)

Photo: Trip by Skyscanner

Another option is The Raffaello Hotel. With a five-star rating on Skyscanner, the hotel is one of the most luxurious in the city. Rooms are currently listed for $99/night. Set in the heart of Chicago, this hotel is close to the Hancock Building, Water Tower Place and the Tribune Tower.

Local restaurant picks

If you're looking to snag a bite at one of Chicago's many quality eateries, here are a few popular culinary destinations from Skyscanner's listings that will help keep you satiated.

Giordano's (730 N. Rush St.)

Photo: Trip by Skyscanner

If you're looking for a local favorite, head to Giordano's, which has an average of 4.3 stars out of 113 reviews on Skyscanner.

"It's tasty and within walking distance from hotels and parks," wrote visitor Ulani. "I got cheese curds, which were yummy. The minestrone soup was chock-full of veggies and tasty. The pizza, as always, was crisp on the crust and ooeey-gooey inside."

The Signature Room at the 95th (875 N. Michigan Ave.)

Photo: Trip by Skyscanner

Another popular dining destination is The Signature Room at the 95th, with 4.5 stars from 65 reviews.

The Signature Room at the 95th, atop the John Hancock Center, offers diners a 360-degree skyline view, with floor-to-ceiling windows. Enjoy a lunch buffet Monday through Saturday, in addition to the à la carte lunch menu. Dinner is served nightly and features seafood, steaks and chops.

"I love this place for the food and the awesome views of Chicago," wrote reviewer geminitraveller. "The classy and cozy ambiance is perfect for a romantic date. It's an expensive place but worth the spend for the unforgettable experience."

The Purple Pig (500 N. Michigan Ave.)

Photo: Trip by Skyscanner

Also worth considering is The Purple Pig.

A collaboration among four top chefs, the Purple Pig specializes in "cheese, swine and wine."

"Every dish was delicious," wrote Maggie. "The fried pig ear came with fried kale, the cheesy broccoli was unique with the tangy cheese sauce, the bone marrow didn't have much bone marrow but came with lots of buttery brioche bread, and meatballs."

Ghirardelli Ice Cream & Chocolate Shop (830 N. Michigan Ave.)

Photo: Trip by Skyscanner

Finally, there's Ghirardelli Ice Cream & Chocolate Shop.

"I love the Ghirardelli ice cream and chocolate selection," wrote Celeny. "The ice cream is the perfect treat for warm summer days."

Featured local attractions

Not sure what to do in Chicago, besides eat and drink? Here are a few recommendations, provided by Skyscanner.

Millennium Park (201 E. Randolph St.)

Photo: Trip by Skyscanner

First up is Millennium Park, which is a large public park and is the most famous section of Grant Park. It is home to most of the park’s highlights, including the Cloud Gate sculpture, nicknamed The Bean. The park is considered one of the largest green roofs in the world, as it was built on top of parking garages and a railroad yard. 

"I love Millennium Park in all seasons," wrote visitor Marcia. "My child enjoys going there for movies and dancing events. It’s worth going to check out."

The Art Institute of Chicago (111 S. Michigan Ave.)

Photo: Trip by Skyscanner

The Art Institute of Chicago is another popular destination.

It is most famous for its Impressionist and Post-Impressionist collections. Some of the more notable works include Monet’s "Haystacks," Toulouse-Lautrec’s "Moulin Rouge" and Edward Hopper’s "Nighthawks."

"It's a simple, quiet indoor space for all ages to relax after shopping or visiting the park," wrote visitor Ulani. "Kids can take part in free workshops, draw, build, read and create a unique journey map for a self-guided museum tour."

Willis Tower (233 S. Wacker Drive)

Photo: Trip by Skyscanner

Finally, consider checking out Willis Tower.

The skyscraper, formerly known as the Sears Tower (a name which is still commonly used), is actually nine square buildings bundled together; an engineering strategy to help the 110-story structure resist Chicago’s infamously high winds. When it finished construction in 1974, it was the world’s tallest building at 1,451 feet.

"There are great views of the city and on a clear day you can see out across Lake Michigan," wrote visitor Yvonne.


This story was created automatically using flight, hotel, and local attractions data, then reviewed by an editor. Click here for more about what we're doing. Got thoughts? Go here to share your feedback.